The invention relates to a new process for preparation of 1,5-dimethylbicyclo[3,2,1]octan-8-ol. More particularly, this invention is directed to a stepwise synthesis technique by which 1,5-dimethylbicyclo[3,2,1]octan-8-ol can be prepared in good yields from readily available starting materials.
1,5-Dimethylbicyclo[3,2,1]octan-8-ol is a compound having high thermal stability which can be used to advantage as a starting material for preparing additives for lubricating oil such as those described in copending U.S. patent application Ser. No. 883,761, filed Mar. 6, 1978. (Common assignee). Further, the compound is also useful as a base material for the preparation of aroma chemicals.
The preparation of 1,5-dimethylbicyclo[3,2,1]octan-8-ol has been described in the literature. Specifically, it is disclosed by J. K. Whitesell, R. S. Matthews and P. A. Solomon in Tetrahedron Letters No. 19, pp. 1549-1552, 1976 that 1,5-dimethylbicyclo[3,2,1]octan-8-ol can be obtained in yield of 50% by reacting 1,5-dimethyl-1,5-cyclooctadiene with a solution of perchloric acid in a mixture of water and dioxane. However, the handling of perchloric acid presents safety hazards and other practical drawbacks. Accordingly, it would be of advantage if a technique could be developed for the preparation of 1,5-dimethylbicyclo[3,2,1]octan-8-ol which uses readily available and easily handleable starting materials while providing good yields of the desired alcohol product.